Signing Manny Ramirez at the 2000 Winter Meetings signaled a new era in Red Sox history

"I'm just tired to see New York always win."

Coming off a fourth World Series win in 15 years, the Red Sox are firmly entrenched among baseball’s elite. Not only has the team been a regular contender in the playoffs, but also in the offseason in the pursuit of free agents.

Few were more important or significant than that of Manny Ramirez on December 12, 2000. The power-hitting outfielder agreed to an eight-year, $160 million deal (then a team record). Completed during the Winter Meetings, the signing of the 28-year-old was a Red Sox statement of intent following the Yankees’ fourth World Series win in five years.

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And it almost didn’t happen.

Only days before, as the usual free agent scrambling was occurring during the Winter Meetings, it appeared Ramirez would be staying with his original team, the Cleveland Indians.

Another proposed deal – which was reportedly contingent on Ramirez coming to the Red Sox – was to send rightfielder Trot Nixon and pitcher Tomo Ohka to the Montreal Expos in exchange for pitcher Dustin Hermanson.

Yet the Red Sox persevered. A unique aspect to Ramirez’s free agent tour that year was that ESPN’s “Outside the Lines” filmed and recorded many of the high-level interactions, providing a retrospective inside look at the process. (Then-ESPN sportswriter Bill Simmons wrote a lengthy piece chronicling some of the unintentionally humorous moments from the behind-the-scenes look, as Red Sox general manager Dan Duquette and Ramirez’s agent, Jeff Moorad, engaged in awkward negotiation).

“The Fellowship of the Miserable is simply unable to come up with anything negative about this latest Red Sox move,” wrote Globe columnist Dan Shaughnessy. He later added of the Red Sox general manager, “Dan Duquette has gone from doofus to genius in less than 24 hours.”

At the beginning of his introductory press conference, Ramirez donned a Red Sox jersey for the first time before giving the thumbs up and saying one word.

It proved to be a masterful signing, as Ramirez lived up to his billing. He smashed 274 home runs for Boston in 1,083 regular season games. He also helped the Red Sox win two World Series titles, and was named MVP of the 2004 Fall Classic (which ended an 86-year drought).

One quote that looks especially interesting to retrospective readers came from then-Globe columnist Michael Holley the day after Ramirez’s press conference.

“Everything is cool. There are no worries. Bill Belichick, Mike Keenan, and Rick Pitino are all temporarily off the hook,” Holley said. “Dan Duquette suddenly looks as good as Brad Pitt.”